Eighteen years after their breakout successand they're back in theaters, too

Almost unthinkable now, 18 years ago, both a writer-director and a performer made career breakthroughs with a film based on a 1928 novel by a titan of modernism about a character who changes genders and lives through four centuries. In her nimble adaptation of Virginia Woolf's Orlando, Sally Potter—who had previously made avant-garde shorts and the feature-length The Gold Diggers (1983), an experimental gloss on Busby Berkeley—created one of cinema's finest page-to-screen transfers, which played at Venice in 1992 and opened New Directors/New Films the following March before its U.S. release in June 1993. Orlando also introduced Tilda Swinton—until then known almost exclusively to art-house cognoscenti for her work with the fiercely uncompromising Derek Jarman—to a larger audience. As the titular poetry-loving nobleman of the very early 17th century who becomes, some 100 years later, a noblewoman, Swinton gives one of the bravura, protean performances that have come to define her career: Her gender metamorphosis was the first of many audacious onscreen transformations, including her speaking Russian-inflected Italian in the current I Am Love.

A month before its updated release on DVD, with Swinton more popular than ever, Sony Pictures Classics is taking the unusual step of re-releasing a new print of Potter's masterpiece in theaters on July 23. This, after Potter's latest, Rage, had the dubious distinction of being the first film to debut on mobile phones last September, leading one to wonder: Was it possible to make more daring films in the early '90s than it is now? Potter is reluctant to generalize: "Before Orlando was released, it met with absolute resistance—just as much resistance as anything I've tried to do subsequently," she says, reminiscing with Swinton at the Bowery Hotel about their sole collaboration the day after MOMA kicked off its Potter tribute. "This particular project was an impossible one and ridiculous to take on."

Undeterred by industry professionals who sniffed that the film was "unmakable," Potter, who wrote her first treatment for Orlando in 1984 and began working with Swinton on the project in 1988, would eventually shoot not just in England but also St. Petersburg, Russia (re-creating Woolf's icy winter on the Thames scenes), and Uzbekistan (a stand-in of sorts for Orlando's journey as an ambassador to Constantinople, condensed in Potter's film). Swinton notes that the very outrageousness in tackling Woolf's gender-bending, time-traveling novel, which she and Potter had both read and adored as teenagers, was "liberating": "Existentially, there's something about a very loved book—there's something about that experience that is very solitary, very private. And the idea of shining a light on it and attempting to render that somehow collectively viable is weird."

Sony Pictures Classics

Swinton recalls the novel as "liberating"

Sylvia Plachy

Although certainly loyal to the bold spirit of its original source, Potter's Orlando is also distinguished by the director's own interventions: adding characters like Jimmy Sommerville's singing angel, upping the gender-play by casting Quentin Crisp as Queen Elizabeth I, giving Orlando not a son but a daughter, and ending the film not in 1928, when Woolf's novel concludes, but 1992. "You can't be over-reverent when you're doing an adaptation," explains Potter. "It doesn't serve the original author well because you're moving into a different medium. But [all changes] have to be done on the basis of knowledge. You can't just hack at something. The thing with Virginia Woolf is, you can't dilute her. So I really studied not only the book, but everything that Virginia Woolf had ever written. The ending had to be done because the novel was so much about ending in the present moment, when she put down her pen. To be true to that principle, we had to take the story up to the moment of finishing the film in 1992. To be true, you have to change things."

Changing is precisely what Swinton worked hard to avoid when her male character wakes up a woman. "Transformation is not about changing," she laughs. "It's about a sustainable spirit." Or, in Potter's equally heady words: "[It's] looking for a state of being-ness through time and space and genders." As Orlando herself says while looking into the camera: "Same person, no difference at all. Just a different sex."

This direct address to the audience, occurring several times throughout the film, became crucial to establishing what Potter refers to as "a state of absolute complicity" and what Swinton calls "personal connection." "I think, cinematically, we had this task, which was to break the picture," Swinton continues. "One goes into a frame, and it's possible to get lost in the picture. And we were continually wanting Orlando to break"—she snaps her fingers here—"out of the picture and make contact with the audience."

Leaping across centuries, Potter's film, while visually opulent, remains free of the fastidious obsession with surface detail that weighs down so many historical epics. "The thing I said again and again and again to the design crew was, 'This is not a period film. This is a film about now-ness,' " Potter says. "It's this skip and a hop through an imagined history that is rooted in an eternal present. And I think that's what makes it look, at any point, fresh."

Did the film, with its deft approach to gender fluidity, strike these two as being ahead of its time? "It didn't feel like it was particularly new," Swinton says. "It felt like it came out of something." Both women mention the importance of the legendary director Michael Powell, who died two years before the movie's premiere but who, as Potter explains, "personally put his support in private behind the project when others were saying it's impossible." Swinton continues: "He told us there was a time when he considered making a film of Orlando. So one can imagine making this film in the 1950s. I don't know whether it ever felt like it was ahead of anything."

Essentially, years—whether 1600, 1928, 1992, or 2010—are meaningless. "By definition, [the film] is out of time because of what it does," Potter says. "It hasn't gone away." She turns to Swinton, laughs, and adds, "Here we are—we're still talking about Orlando. It'll never end." Then they head off to a photo shoot, walking side by side, their arms around each other's waists.